Compound and organic light emitting device using the compound

ABSTRACT

A novel mono(benzo[k]fluoranthene) compound having a molecular structure containing at least one condensed ring aromatic group which is tricyclic or more at any of 7- to 9-positions of benzo[k]fluoranthene. Also an organic light emitting device including at least a pair of electrodes formed of an anode and a cathode, and a layer formed of an organic compound, the layer being interposed between the pair of electrodes, in which the layer formed of an organic compound contains a compound represented by the following structural formula. An organic light emitting device in which the layer is a light emitting layer.

This application is a continuation of application Ser. No. 12/295,240,filed Sep. 29, 2008, which is a national phase application based onPCT/JP2007/055583, filed Mar. 13, 2007, the entire disclosure of each ofwhich is incorporated herein by reference.

TECHNICAL FIELD

The present invention relates to a novel compound and an organic lightemitting device using the compound, and more specifically, to an organiclight emitting device using the novel compound in its light emittinglayer.

BACKGROUND ART

An organic light emitting device includes: an anode; a cathode; and athin film containing a fluorescent organic compound or a phosphorescentorganic compound, the thin film being interposed between the anode andthe cathode. An electron and a hole are injected from the respectiveelectrodes. As a result, the organic light emitting device generates anexciton of the fluorescent organic compound or of the phosphorescentorganic compound. The device utilizes light to be radiated when theexciton returns to its ground state. Recent progress in an organic lightemitting device is remarkable. The organic light emitting device hassuch characteristics that it can be turned into a thin, lightweightlight emitting device which: provides high luminance at a low appliedvoltage; and has the diversity of a luminous wavelength and high-speedresponsiveness. The characteristics suggest that the light emittingdevice may be used in a wide variety of applications.

However, the conventional organic light emitting device requires opticaloutput with additionally higher luminance or higher conversionefficiency. In addition, the organic light emitting device stillinvolves many problems in terms of durability such as a change with timedue to long-term use and deterioration due to, for example, anatmospheric gas containing oxygen or humidity. Further, when it isattempted that the device is applied to a full-color display and thelike, each of blue light, green light, and red light must be emitted ata good color purity. However, problems concerning the emission have notbeen sufficiently solved yet.

In addition, examples of a patent document describing a compound havinga benzo[k]fluoranthene skeleton include Japanese Patent ApplicationLaid-Open Nos. H10-189247, 2005-235787, 2000-007587, 2000-007594 and2005-068087.

DISCLOSURE OF THE INVENTION

An object of the present invention is to provide a novelmono(benzo[k]fluoranthene) compound formed of a molecular structurecontaining at least one condensed ring aromatic group which is tricyclicor more at any of 7- to 9-positions of benzo[k]fluoranthene.

Another object of the present invention is to provide an organic lightemitting device which uses the above compound and which has an opticaloutput with extremely high efficiency and extremely high brightness.Another object of the present invention is to provide an organic lightemitting device having extremely high durability. Another object of thepresent invention is to provide an organic light emitting device whichcan be easily produced at a relatively low cost.

According to the present invention, there is provided amono(benzo[k]fluoranthene) compound represented by the following generalformula (I):

where R₁ to R₁₂ each represent a hydrogen atom, a linear or branchedalkyl group, a substituted or unsubstituted aryl group, or a substitutedor unsubstituted heterocyclic group, provided that at least one of R₇,R₈, and R₉ represents a substituted or unsubstituted condensed ringaromatic group which is tricyclic or more.

Further, according to the present invention, there is provided amono(benzo[k]fluoranthene) compound, in which one or more of R₁₀, R₁₁,and R₁₂ in the general formula (I) each represent a substituted orunsubstituted aryl group, or a substituted or unsubstituted heterocyclicgroup.

Further, according to the present invention, there is provided amono(benzo[k]fluoranthene) compound, in which one or more of R₁₀, R₁₁,and R₁₂ in the general formula (I) each represent a substituted orunsubstituted condensed ring aromatic group which is tricyclic or more.

Further, according to the present invention, there is provided amono(benzo[k]fluoranthene) compound, in which R₇ in the general formula(I) represents a substituted or unsubstituted fluorenyl group.

Further, according to the present invention, there is provided amono(benzo[k]fluoranthene) compound which is represented by thefollowing general formula (II):

where:

R₁ to R₆, and R₈ to R₁₂ each represent a hydrogen atom, a linear orbranched alkyl group, a substituted or unsubstituted aryl group, or asubstituted or unsubstituted heterocyclic group; and

R₂₁ and R₂₂ each represent a hydrogen atom, an alkyl group, asubstituted or unsubstituted aryl group, or a substituted orunsubstituted heterocyclic group, and R₂₁ and R₂₂ may be identical to ordifferent from each other; R₂₃ and R₂₄ each represent a hydrogen atom,an alkyl group, a substituted or unsubstituted aryl group, a substitutedor unsubstituted heterocyclic group, a substituted amino group, or ahalogen atom; a represents an integer of 1 to 3, and b represents aninteger of 1 to 4; and, when the number of any one of R₂₃ and R₂₄ is twoor more, R₂₃'s or R₂₄'s may be identical to or different from eachother.

Further, according to the present invention, there is provided amono(benzo[k]fluoranthene) compound, in which themono(benzo[k]fluoranthene) compound is represented by the followinggeneral formula (III):

where:

R₁ to R₆, and R₆ to R₁₁ each represent a hydrogen atom, a linear orbranched alkyl group, a substituted or unsubstituted aryl group, or asubstituted or unsubstituted heterocyclic group; and

R₂₁, R₂₂, R₂₅, and R₂₆ each represent a hydrogen atom, an alkyl group, asubstituted or unsubstituted aryl group, or a substituted orunsubstituted heterocyclic group, and R₂₁, R₂₂, R₂₅, and R₂₆ may beidentical to or different from each other; R₂₃, R₂₄, R₂₇, and R₂₈ eachrepresent a hydrogen atom, an alkyl group, a substituted orunsubstituted aryl group, a substituted or unsubstituted heterocyclicgroup, a substituted amino group, or a halogen atom; a and c eachrepresent an integer of 1 to 3, and b and d each represent an integer of1 to 4, and, when the number of any one of R₂₃, R₂₄, R₂₇, and R₂₈ is twoor more, R₂₃'s, R₂₄'s, R₂₇'s, and R₂₈'s may be identical to or differentfrom each other.

Further, according to the present invention, there is provided amono(benzo[k]fluoranthene) compound, in which R₇ in the general formula(I) represents a substituted or unsubstituted fluoranthenyl group.

Further, according to the present invention, there is provided amono(benzo[k]fluoranthene) compound which is represented by thefollowing general formula (IV):

where:

R₁ to R₆, and R₈ to R₁₂ each represent a hydrogen atom, a linear orbranched alkyl group, a substituted or unsubstituted aryl group, or asubstituted or unsubstituted heterocyclic group; and

R₂₉ and R₃₀ each represent a hydrogen atom, an alkyl group, asubstituted or unsubstituted aryl group, a substituted or unsubstitutedheterocyclic group, a substituted amino group, or a halogen atom; erepresents an integer of 1 to 5, and f represents an integer of 1 to 4;and, when the number of any one of R₂₉ and R₃₀ is two or more, R₂₉'s orR₃₀'s may be identical to or different from each other.

According to the present invention, there is provided amono(benzo[k]fluoranthene) compound which is represented by thefollowing general formula (V):

where:

R₁ to R₆, and R₈ to R₁₁ each represent a hydrogen atom, a linear orbranched alkyl group, a substituted or unsubstituted aryl group, or asubstituted or unsubstituted heterocyclic group; and

R₂₉ to R₃₂ each represent a hydrogen atom, an alkyl group, a substitutedor unsubstituted aryl group, a substituted or unsubstituted heterocyclicgroup, a substituted amino group, or a halogen atom; e and g eachrepresent an integer of 1 to 5, and f and h each represent an integer of1 to 4; and, when the number of any one of R₂₉, R₃₀, R₃₁, and R₃₂ is twoor more, R₂₉'s, R₃₀'s, R₃₁'s, or R₃₂'s may be identical to or differentfrom each other.

Specific examples of the substituents in the general formulae (I), (II),(III), (IV), and (V) are shown below; provided that the examples aremerely representative examples, and the present invention is not limitedto those examples.

As the alkyl group, there may be given a methyl group, an ethyl group, anormal propyl group, an isopropyl group, an normal butyl group, atertiary butyl group, an octyl group, a cyclohexyl group, atrifluoromethyl group, and the like.

Examples of the aryl group include a phenyl group, a biphenyl group, aterphenyl group, a fluorenyl group, a naphtyl group, a fluoranthenylgroup, an anthryl group, a phenanthryl group, a pyrenyl group, atetracenyl group, a pentacenyl group, a triphenylenyl group, and aperylenyl group.

As the heterocyclic group, there may be given a thienyl group, apyrrolyl group, a pyridyl group, an oxazolyl group, an oxadiazolylgroup, a thiazolyl group, a thiadiazolyl group, and the like.

As the substituted amino group, there may be given a dimethylaminogroup, a diethylamino group, a dibenzylamino group, a diphenylaminogroup, a ditolylamino group, a dianisolylamino group, and the like. Asthe halogen atom, there may be given fluorine, chlorine, bromine,iodine, and the like.

Examples of a condensed ring aromatic group which is tricyclic or moreinclude a fluorenyl group, a pyrenyl group, a fluoranthenyl group, abenzofluoranthenyl group, a tetracenyl group, a pentacenyl group, atriphenylenyl group, a perylenyl group, and a chrysenyl group.

Examples of a condensed ring aromatic skeleton which is tetracyclic ormore include a pyrene skeleton, a fluoranthene skeleton, abenzofluoranthene skeleton, a tetracene skeleton, a triphenyleneskeleton, and a chrysene skeleton.

Examples of substituents which the above-mentioned substituents may haveinclude: alkyl groups such as a methyl group, an ethyl group, and apropyl group; aryl groups such as a phenyl group and a biphenyl group;heterocyclic groups such as a thienyl group, a pyrrolyl group, and apyridyl group; amino groups such as a dimethylamino group, adiethylamino group, a dibenzylamino group, a diphenylamino group, aditolylamino group, and a dianisolylamino group; and halogen atoms suchas fluorine, chlorine, bromine, and iodine.

Further, according to the present invention, there is provided anorganic light emitting device including: a pair of electrodes formed ofan anode and a cathode; and an organic compound layer being interposedbetween the pair of electrodes, in which the organic compound layercontains at least one kind of compound represented by theabove-mentioned general formula (I).

Further, according to the present invention, there is provided anorganic light emitting device in which the organic compound layer is alight emitting layer. Further, according to the present invention, thereis provided an organic light emitting device in which the light emittinglayer is formed of at least two kinds of compounds including a host anda guest.

In addition, according to the present invention, there is provided anorganic light emitting device including: a pair of electrodes formed ofan anode and a cathode; and an organic compound layer placed between thepair of electrodes, in which the organic compound layer contains a firstcompound having a benzo[k]fluoranthene skeleton and a second compoundhaving a condensed ring aromatic skeleton which is tetracyclic or more,the second compound having an energy gap larger than that of the firstcompound.

Further, there is provided an organic light emitting device, in whichthe condensed ring aromatic skeleton which is tetracyclic or more is oneof a pyrene skeleton and a fluoranthene skeleton.

Further, there is provided an organic light emitting device, in whichthe first compound is a mono(benzo[k]fluoranthene) compound representedby the general formula (I).

Further, there is provided an organic light emitting device, in whichthe first compound and the second compound have the same condensed ringaromatic skeleton.

Further, there is provided an organic light emitting device, in whichthe condensed ring aromatic skeleton includes a fluorene skeleton.

Further, there is provided an organic light emitting device, in whichthe organic light emitting device includes an electroluminescence devicethat emits light by applying a voltage between the pair of electrodes.

The compound of the present invention has a high glass transitiontemperature, and the light emitting device of the present inventionusing the compound of the present invention as a host or guest for itslight emitting layer can realize highly efficient light emission withgood color purity. In addition, the device is an excellent devicebecause the device has high heat stability, and keeps high brightnessfor a time period longer than that in the case where a conventionallyused compound is used.

Further features of the present invention will become apparent from thefollowing description of exemplary embodiments with reference to theattached drawings.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 is a sectional view showing an example of an organic lightemitting device of the present invention;

FIG. 2 is a sectional view showing another example of the organic lightemitting device of the present invention;

FIG. 3 is a sectional view showing still another example of the organiclight emitting device of the present invention;

FIG. 4 is a sectional view showing yet another example of the organiclight emitting device of the present invention;

FIG. 5 is a sectional view showing still yet another example of theorganic light emitting device of the present invention;

FIG. 6 is a sectional view showing still yet another example of theorganic light emitting device of the present invention;

FIG. 7 is a view showing the emission spectrum of a solution of each ofCompound No. A-1 of the present invention and Comparative Compound 13 intoluene having a concentration of 1×10⁻⁵ mol/l; and

FIG. 8 is a view showing the emission spectrum and absorption spectrumof a thin film of each of Compound No. A-1 of the present invention andComparative Compound 13 having a concentration of 1×10⁻⁵ mol/l.

BEST MODE FOR CARRYING OUT THE INVENTION

Hereinafter, the present invention will be described in detail.

When a light emitting layer in an organic light emitting device isformed of a carrier transporting host material and a guest, a mainprocess for light emission includes the following several steps:

1. the transport of an electron or a hole in the light emitting layer;

2. the generation of an exciton of the host material;

3. the transfer of excitation energy between host material molecules;and

4. the movement of the excitation energy from the host material to theguest.

Desired energy movement in each step, and light emission occur incompetition with various deactivation steps.

Needless to say, the emission quantum yield of a light emission centralmaterial itself must be large in order that the luminous efficiency ofan organic light emitting device may be improved. However, theefficiency with which energy movement between host and host molecules orbetween host and guest molecules can be performed is also of greatconcern. In addition, the deterioration of light emission due toenergization is assumed to be related to a change in environmentsurrounding a light emitting material due to at least the light emissioncentral material itself or a molecule around the light emission centralmaterial, though no causes for the deterioration have been revealed atpresent.

In view of the foregoing, the inventors of the present invention havemade various studies. As a result, the inventors have found that adevice using a compound represented by the general formula (I) as a hostor guest for its light emitting layer emits light with high efficiency,keeps high brightness for a long time period, and shows smalldeterioration of light emission due to energization.

One possible cause for the deterioration of the light emission due tothe energization may be the deterioration of the thin-film shape of thelight emitting layer. The deterioration of the thin-film shape mayresult from the crystallization of the organic thin film due to, forexample, the temperature of an environment in which the device is drivenor heat generation at the time of the driving of the device. Thecrystallization may originate from the low glass transition temperatureof a material for the thin film, so it is desired that an organic ELmaterial have a high glass transition temperature. An improvement indurability of an organic light emitting device can be expected from thecompound represented by the general formula (I) of the present inventionbecause the compound has a high glass transition temperature.

The compound of the present invention will be described.

Benzo[k]fluoranthene is known to be a compound having a quantum yield of1.0 in a dilute solution (J. Photochem. 18, 9-17 (1982)). However, thecompound is extremely apt to undergo concentration quenching, and abenzo[k]fluoranthene thin film does not emit light. Accordingly, highefficiency may not be obtained from benzo[k]fluoranthene itself whenbenzo[k]fluoranthene is used in an organic EL device. In addition,benzo[k]fluoranthene contains a large amount of ultraviolet emissioncomponents each having a maximum luminous wavelength of 400 nm; thewavelength is not optimum enough to allow benzo[k]fluoranthene to beused as a blue light emitting material. When benzo[k]fluoranthene isused as a light emitting material in a light emitting device, the deviceis doped with the light emitting material at a relatively highconcentration of about 0.1 to 20 wt % with respect to a host material.Accordingly, unlike a state where the concentration of the lightemitting material is low, the light emitting properties of the lightemitting material in a solid film are of extreme importance. Inaddition, a compound having a large amount of emission components eachhaving a maximum luminous wavelength of 450 to 460 nm is expected toemit blue light with high efficiency and good color purity when thecompound is used as a blue light emitting material for a display.

The compound of the present invention has one benzo[k]fluoranthene sitein its molecule. Accordingly, the probability that benzo[k]fluoranthenesites collide with each other in the film of a light emitting device inwhich the compound is dispersed may be reduced, concentration quenchingmay be suppressed, and highly efficient light emission may be expected.Further, a relatively large, condensed ring aromatic group which istricyclic or more is introduced into any of 7- to 9-positions ofbenzo[k]fluoranthene, so the suppression of concentration quenching maybe expected owing to the steric hindrance of a substituent. Further, thepresence of a substituted or unsubstituted aryl group or a substitutedor unsubstituted heterocyclic group at any of 10- to 12-positions ofbenzo[k]fluoranthene may improve not only the ease with which thecompound is synthesized but also the stability of the compound. Inaddition, a compound having a condensed ring aromatic group which istricyclic or more at 7-position of benzo[k]fluoranthene is particularlypreferable because a substituent may show large steric hindrance at7-position of benzo[k]fluoranthene. A compound having a condensed ringaromatic group which is tricyclic or more at each of 7- and 12-positionsof benzo[k]fluoranthene is also preferable because a substituent maysimilarly show large steric hindrance at 12-position ofbenzo[k]fluoranthene. In addition, from the viewpoint of a luminouswavelength, the lengthening of a wavelength can be expected from theproperty with which an electron is donated to benzo[k]fluoranthene. Inaddition, from the viewpoint of a quantum yield, a compound having, as asubstituent, a condensed ring aromatic structure which is tricyclic ormore and which has a large oscillator strength is preferable for therealization of a high quantum yield. In addition, among the condensedring aromatic groups each of which is tricyclic or more, a fluorenylgroup is a particularly preferable condensed ring aromatic group whichis tricyclic or more because the group is expected to show sterichindrance by a substituent attached to the carbon atom at 9-position ofthe group. A fluoranthenyl group is also particularly preferable becauseof the following reason: when benzo[k]fluoranthene is substituted by thefluoranthenyl group having a skeleton similar to that ofbenzo[k]fluoranthene, the highest occupied molecular orbital (HOMO) andlowest unoccupied molecular orbital (LUMO) of a molecule of theresultant compound expand over the entirety of the molecule, so animprovement in stability of the molecule can be expected.

In addition, as described above, a compound to be used in an organic ELdevice is required to have a high glass transition temperature. Ingeneral, a material having a larger molecular weight has a higher glasstransition temperature. When a substituent to be introduced intobenzo[k]fluoranthene is limited to a small aromatic ring such as aphenyl group or a tolyl group, the resultant compound has a smallmolecular weight, so a high glass transition temperature may not beexpected. In addition, the introduction of only an alkyl group mayreduce the glass transition temperature of the resultant compound,though the introduction increases the molecular weight of the compound.Accordingly, as the substituent to be introduced intobenzo[k]fluoranthene, the condensed ring aromatic group which istricyclic or more used in the present invention is preferable from theviewpoint of a glass transition temperature.

Accordingly, the compound of the present invention is a compoundrepresented by any one of the following general formulae (I) to (V).

In the formulae, R₁ to R₁₂, R₂₁ and R₂₂, and R₂₅ and R₂₆ eachindependently represent a hydrogen atom; an alkyl group such as a methylgroup, an ethyl group, a normal propyl group, an isopropyl group, anormal butyl group, a tertiary butyl group, an octyl group, a cyclohexylgroup, or a trifluoromethyl group; an aryl group such as a phenyl group,a biphenyl group, a terphenyl group, a fluorenyl group, a naphthylgroup, a fluoranthenyl group, an anthryl group, a phenanthryl group, apyrenyl group, a tetracenyl group, a pentacenyl group, a triphenylenylgroup, or a perylenyl group; or a heterocyclic group such as a thienylgroup, a pyrrolyl group, a pyridyl group, an oxazolyl group, anoxadiazolyl group, a thiazolyl group, or a thiadiazolyl group, providedthat at least one of R₇, R₈, and R₉ represents a condensed ring aromaticgroup which is tricyclic or more such as a fluorenyl group, a pyrenylgroup, a fluoranthenyl group, a benzofluoranthenyl group, a tetracenylgroup, a pentacenyl group, a triphenylenyl group, a perylenyl group, ora chrysenyl group, and one or more of R₁₀, R₁₁, and R₁₂ each representan aryl group such as a phenyl group, a biphenyl group, a terphenylgroup, a fluorenyl group, a naphthyl group, a fluoranthenyl group, ananthryl group, a phenanthryl group, a pyrenyl group, a tetracenyl group,a pentacenyl group, a triphenylenyl group, or a perylenyl group; or aheterocyclic group such as a thienyl group, a pyrrolyl group, a pyridylgroup, an oxazolyl group, an oxadiazolyl group, a thiazolyl group, or athiadiazolyl group.

R₂₁ and R₂₂, and R₂₅ and R₂₆ each preferably represent an alkyl group interms of the stability of the carbon atom at 9-position of a fluorenylgroup against a radical. In addition, an increase in the length of analkyl chain at 9-position of the fluorenyl group may reduce the glasstransition temperature. Accordingly, R₂₁ and R₂₂, and R₂₅ and R₂₆ eachmore preferably represent an alkyl group having a short carbon chainsuch as a methyl group or an ethyl group. In addition, R₂₁ and R₂₂, andR₂₅ and R₂₆, which may be identical to or different from one another,are preferably identical to one another from the viewpoint of the easewith which the compound is synthesized.

R₂₃ and R₂₄, R₂₇ and R₂₈, and R₂₉ to R₃₂ each represent a hydrogen atom,an alkyl group such as a methyl group, an ethyl group, a normal propylgroup, an isopropyl group, a normal butyl group, a tertiary butyl group,an octyl group, a cyclohexyl group, or a trifluoromethyl group; an arylgroup such as a phenyl group, a biphenyl group, a terphenyl group, afluorenyl group, a naphthyl group, a fluoranthenyl group, an anthrylgroup, a phenanthryl group, a pyrenyl group, a tetracenyl group, apentacenyl group, a triphenylenyl group, or a perylenyl group; aheterocyclic group such as a thienyl group, a pyrrolyl group, a pyridylgroup, an oxazolyl group, an oxadiazolyl group, a thiazolyl group, or athiadiazolyl group; an amino group such as a dimethylamino group, adiethylamino group, a dibenzylamino group, a diphenylamino group, aditolylamino group, or a dianisolylamino group; or a halogen atom suchas fluorine, chlorine, bromine, or iodine. a and c each represent aninteger of 1 to 3, b and d each represent an integer of 1 to 4, e and geach represent an integer of 1 to 5, and f and h each represent aninteger of 1 to 4. When the number of any one of R₂₃ and R₂₄, R₂₇ andR₂₉, and R₂₉ to R₃₂ is two or more, R₂₃'s, R₂₄'s, R₂₇'s, R₂₈'s, R₂₉'s,R₃₀'s, R₃₁'s, or R₃₂'s may be identical to or different from each other.

Hereinafter, specific examples of the structural formula of an organiccompound to be used in the present invention are shown below. It shouldbe noted that the examples are merely representative examples, and thepresent invention is not limited to the examples.

Next, an organic light emitting device of the present invention will bedescribed in detail.

The organic light emitting device of the present invention is an organiclight emitting device having at least one pair of electrodes formed ofan anode and a cathode, and an organic compound layer interposed betweenthe pair of electrodes, and the organic compound layer contains acompound represented by the general formula (I).

The organic light emitting device of the present invention may befurther provided with another organic compound layer in addition to theabove organic compound layer.

In the organic light emitting device of the present invention, the aboveorganic compound layer may further contain another compound in additionto the compound represented by the general formula (I).

At least a light emitting layer among the layers each containing anorganic compound of the organic light emitting device of the presentinvention preferably contains at least one kind of the above describedcompounds. In addition, in an organic light emitting device having alight emitting layer formed of two or more compounds including a hostand a guest, the host or the guest is preferably the above describedcompound. The term “guest” as used in the present invention refers to acompound that mainly emits light in response to recombination between ahole and an electron in the light emitting region of the organic lightemitting device. The guest is incorporated into another compound (host)of which the light emitting region is formed.

The content of the compound represented by the general formula (I)according to the present invention to be used as the guest is preferably50 wt % or less, more preferably 0.1 wt % or more to 30 wt % or less, orparticularly preferably 0.1 wt % or more to 15 wt % or less.

The content of the compound represented by the general formula (I)according to the present invention to be used as the host is preferably50 wt % or less, more preferably 70 wt % or more to 99.9 wt % or less,or particularly preferably 85 wt % or more to 99.9 wt % or less.

On the other hand, when the compound represented by the general formula(I) according to the present invention is used as a host compound, theguest is not particularly limited, and, for example, a compound to bedescribed later can be appropriately used depending on, for example, adesired luminescent color. In addition, the light emitting layer may bedoped with a hole transporting compound, an electron transportingcompound, or the like as required together with the guest.

The compound of the present invention, which may be used only in thelight emitting layer among the organic compound layers, can be used in,for example, a hole injecting layer, a hole transporting layer, anelectron injecting layer, an electron transporting layer, or an electronblocking layer in addition to the light emitting layer as required.

In the organic light emitting device of the present invention, thecompound represented by the above general formula (I) is formed betweenthe anode and the cathode by a vacuum deposition method or a solutioncoating method. The thickness of the organic layer may be smaller than10 μm, preferably 0.5 μm or less, or more preferably 0.01 μm or more to0.5 μm or less.

FIGS. 1, 2, 3, 4, 5 and 6 each show a preferable example of the organiclight emitting device of the present invention.

First, provided are a substrate 1, an anode 2, a light emitting layer 3,a cathode 4, a hole transport layer 5, an electron transport layer 6, ahole injection layer 7, and a hole/exciton blocking layer 8.

FIG. 1 is a sectional view showing an example of an organic lightemitting device according to the present invention. As shown in FIG. 1,the organic light emitting device has a structure in which the anode 2,the light-emitting layer 3, and the cathode 4 are provided on thesubstrate 1 in this order. In this example, the light emitting deviceincluding a compound having all of hole-transporting property,electron-transporting property, and light-emitting property or includingcompounds having the respective properties in combination, is useful.

FIG. 2 is a sectional view showing another example of the organic lightemitting device according to the present invention. As shown in FIG. 2,the organic light emitting device has a structure in which the anode 2,the hole transport layer 5, the electron transport layer 6, and thecathode 4 are provided on the substrate 1 in this order. In thisexample, the following case is useful. That is, a light-emittingsubstance whose material has at least one of hole-transporting propertyand electron-transporting property is used for each layer, and thelight-emitting substance is used in combination with a non-illuminanthole-transporting substance or electron-transporting substance. In thiscase, the light-emitting layer is formed of either the hole transportlayer 5, or the electron transport layer 6.

FIG. 3 is a sectional view showing still another example of the organiclight emitting device according to the present invention. As shown inFIG. 3, the organic light emitting device has a structure in which theanode 2, the hole transport layer 5, the light emitting layer 3, theelectron transport layer 6, and the cathode 4 are provided on thesubstrate 1 in this order. This organic light emitting device has acarrier-transporting function and a light-emitting function which areseparated. This device may be used in combination with compounds eachhaving hole-transporting property, electron-transporting property, orlight-emitting property as appropriate, thereby allowing a substantialincrease in freedom of choice in material to be used. Further, variouscompounds having different emission wavelengths can be used, therebyallowing an increase in variety of luminescent colors. Further, luminousefficiency may be improved by efficiently trapping each carrier orexciton in the light-emitting layer provided in the middle of thedevice.

FIG. 4 is a sectional view showing yet another example of the organiclight emitting device according to the present invention. The organiclight emitting device of FIG. 4 has a structure shown in FIG. 3 exceptthat the hole-injecting layer 7 is inserted into a side of the anode.This structure is effective for improving adhesiveness between the anodeand the hole transport layer or for improving hole-injecting property,which is effective in lowering a voltage to be applied to the device.

Each of FIGS. 5 and 6 is a sectional view showing still yet anotherexample of the organic light emitting device according to the presentinvention. The organic light emitting device of FIG. 5 has a structureshown in FIG. 3 except that a layer (the hole/exciton-blocking layer 8)for blocking travel of a hole or exciton to a side of the cathode isinserted between the light-emitting layer and the electron transportlayer. The organic light emitting device of FIG. 6 has a structure shownin FIG. 4 except that a layer (the hole/exciton-blocking layer 8) forblocking travel of a hole or exciton to a side of the cathode isinserted between the light-emitting layer and the electron transportlayer. Each of those structures uses a compound having an extremely highionization potential in the hole/exciton-blocking layer 8 and iseffective for improving luminous efficiency.

However, FIGS. 1, 2, 3, 4, 5 and 6 each show a basic device structure,and the structure of the organic light emitting device using thecompound of the present invention is not limited to the structuresdescribed above. For example, the organic light emitting device of thepresent invention may have any one of various layer structuresincluding: a structure having an insulating layer provided at aninterface between the electrode and the organic layer; a structurehaving an adhesive layer or an interference layer provided; and astructure in which a hole transport layer is composed of two layers withdifferent ionization potentials.

The compound shown in the formula (I) of the present invention may beused for any of the structures shown in FIGS. 1, 2, 3, 4, 5 and 6.

In the present invention, the compound represented by the generalformula (I) is used as a constituent component for the light emittinglayer; a conventionally known hole transporting compound, luminouscompound, electron transporting compound, or the like can be usedtogether with the compound as required.

Hereinafter, examples of those compounds are shown.

Hole Transporting Compounds

Hole Transporting Compounds

Electron-Transporting Light-Emitting Materials

Electron-Transporting Light-Emitting Materials

Light Emitting Materials

Light Emitting Materials

Light-Emitting Layer Matrix Materials and Electron-TransportingMaterials

Light-Emitting Layer Matrix Materials and Electron-TransportingMaterials

Polymeric Hole Transporting Materials

Polymeric Hole Transporting Materials

Polymeric Light Emitting Materials and Charge Transporting Materials

In the organic light emitting device according to the present invention,the layer containing the compound shown in the formula (I) and layerscontaining other organic compounds may be formed generally by a vacuumdeposition method or by a coating method in which the compound isdissolved in an appropriate solvent. In film formation by the coatingmethod, in particular, a film may be formed by using the compound incombination with an appropriate binder resin.

The binder resin may be selected from a wide variety of binder resins.Examples of the binder resin include, but not limited to: a polyvinylcarbazole resin; a polycarbonate resin; a polyester resin; a polyarylateresin; a polystyrene resin; an acrylic resin; a methacrylic resin; abutyral resin; a polyvinyl acetal resin; a diallyl phthalate resin; aphenol resin; an epoxy resin; a silicone resin; a polysulfone resin; anda urea resin. These resins may be used alone, or in combination of atleast two kinds thereof as a homopolymer or copolymer.

An anode material may have as large a work function as possible, andexamples thereof include: a metal simple substance such as gold,platinum, nickel, palladium, cobalt, selenium, or vanadium; an alloythereof; and a metal oxide such as tin oxide, zinc oxide, indium tinoxide (ITO), or indium zinc oxide. Further, a conductive polymer such aspolyaniline, polypyrrole, polythiophene, or polyphenylene sulfide mayalso be used. Each of those electrode materials may be used alone, ortwo or more kinds thereof may be used in combination.

Meanwhile, a cathode material may have a small work function, andexamples thereof include: a metal simple substance such as lithium,sodium, potassium, cesium, calcium, magnesium, aluminum, indium, silver,lead, tin, or chromium; and an alloy of two or more kinds thereof. Ametal oxide such as indium tin oxide (ITO) may also be used. Further,the cathode may have a single layer structure or a multilayer structure.

The substrate to be used in the present invention is not particularlylimited, but examples thereof include: an opaque substrate such as ametallic substrate or a ceramics substrate; and a transparent substratesuch as a glass substrate, a quartz substrate, or a plastic sheetsubstrate. In addition, the substrate may have a color filter film, afluorescent color converting filter film, a dielectric reflection film,or the like for controlling luminescent color.

Further, a protective layer or a sealing layer may be formed on thefabricated device to prevent contact between the device and oxygen,moisture, or the like. Examples of the protective layer include: adiamond thin film; a film formed of an inorganic material such as metaloxide or metal nitride; a polymer film formed of a fluorine resin,polyparaxylene, polyethylene, a silicone resin, a polystyrene resin, orthe like; and a photo-curable resin. Further, the device itself may becovered with glass, a gas-impermeable film, a metal, or the like andpackaged with an appropriate sealing resin.

In addition, the present invention is characterized in that the lightemitting region contains a compound having a benzo[k]fluorantheneskeleton as a guest material and a compound having a condensed ringhydrocarbon skeleton which is tetracyclic or more as a host material.Examples of the condensed ring hydrocarbon skeleton which is tetracyclicor more include a pyrene skeleton, a fluoranthene skeleton, abenzofluoranthene skeleton, a tetracene skeleton, a triphenyleneskeleton, and a chrysene skeleton. Of those, the pyrene skeleton or thefluoranthene skeleton is preferable from the viewpoints of a band gapand carrier transporting property.

Examples of a compound having a pyrene skeleton include, but not limitedto, the following materials.

In addition, the compound having a benzo[k]fluoranthene skeleton as theguest used in the present invention is not particularly limited; acompound represented by any of the above general formulae (I) to (V) ofthe present invention is preferably used as the compound.

Further, the host and the guest preferably have the same condensed ringaromatic structure. The introduction of the same condensed ring aromaticstructure into the molecular structures of the materials, that is, thehost and the guest improves compatibility between the host and theguest, whereby a light emitting device having good durability may beachieved. Examples of the above condensed ring aromatic structureinclude a naphthalene skeleton, a fluorene skeleton, a pyrene skeleton,a fluoranthene skeleton, a benzofluoranthene skeleton, a tetraceneskeleton, a triphenylene skeleton, and a chrysene skeleton. Of those,the fluoranthene skeleton is particularly preferable from the viewpointsof a band gap and an oscillator strength.

EXAMPLES

Hereinafter, the present invention will be described more specificallyby way of examples. However, the present invention is not limited tothese examples.

It should be noted that a benzo[k]fluoranthene derivative represented bya general formula (I) can be produced in accordance with the followingproduction method by, for example, a Diels-Alder reaction betweenCompound 1 and Compound 2 or a Diels-Alder reaction between Compound 3and Compound 4.

Example 1

Synthesis of Exemplified Compound No. A-1

(1-1) Synthesis of Synthetic Intermediate Compound 6

41 g (0.273 mol) of 2-carboxybenzaldehyde (Compound 5), 410 mL ofdioxane, 80 mL of iodomethane, and 82 mL (0.328 mol) of a 4N aqueoussolution of sodium hydroxide were added to a 1-L reaction vessel. Thesolution was vigorously stirred at 70° C. for 16 hours. Dioxane wasremoved under reduced pressure, and 200 mL of distilled water was addedto the solution, followed by extraction with ethyl acetate (200mL×twice). An organic layer was collected, washed with saturated sodiumbicarbonate water, distilled water, and a saturated salt solution, anddried with anhydrous MgSO₄. After that, the solution was condensed,whereby 43 g of a colorless liquid was obtained. The liquid was purifiedby means of silica gel column chromatography (mobile phase; hexane:ethylacetate=3:1), whereby 37.7 g (0.230 mol, yield=84%) of Compound 6 as acolorless liquid were obtained.

(1-2) Synthesis of Synthetic Intermediate Compound 7

58.5 g (183 mmol) of 2-iodo-9,9-dimethylfluorene and 600 mL of diethylether were added to a 1-L reaction vessel. The solution was cooled to−78° C., and 116 mL (183 mmol) of a solution of n-butyllithium in hexanehaving a concentration of 1.57 mol/L was added to the solution over 10minutes. After the solution had been stirred at the temperature for 30minutes, Compound 6 (15 g, 91.3 mmol) dissolved in 100 mL of diethylether and cooled to −20° C. was added to the solution in one stroke. Thesolution was heated to room temperature while a cooling bath wasattached, and 300 mL of 10% ammonia water was added to the suspension,followed by extraction with ethyl acetate (200 mL×twice). An organiclayer was collected, washed with distilled water and a saturated saltsolution, and dried with anhydrous MgSO₄. After that, the solution wascondensed and dried in a high vacuum, whereby 53.6 g of Compound 7 as atan solid was obtained.

(1-3) Synthesis of Exemplified Compound No. A-1

Compound 7 as a solid was loaded into a 1-L reaction vessel, and 600 mLof xylene, 5.2 g (27.3 mol) of p-toluenesulfonic acid, and 13.9 g (91.3mmol) of acenaphthylene were added to the vessel. The solution wasvigorously stirred at 150° C. for 36 hours. Xylene was removed underreduced pressure, and 100 mL of saturated sodium bicarbonate water and400 mL of distilled water were added to the solution, followed byextraction with chloroform (500 mL×twice). An organic layer wascollected, washed with saturated sodium bicarbonate water, distilledwater, and a saturated salt solution, and dried with anhydrous MgSO₄.After that, the desiccant was separated by filtration. 600 g of silicagel was added to the filtrate, and the solvent was condensed andremoved, whereby a black silica gel carrier was obtained. The carrierwas purified by means of silica gel column chromatography (mobile phase;chloroform:hexane=1:3 to chloroform:hexane=1:1), whereby a reddish brownsolid was obtained. The solid was suspended in a small amount ofchloroform, and diethyl ether was added to the suspension to precipitatea crystal. The crystal was taken by filtration and purified by means ofsilica gel column chromatography (mobile phase; chloroform:hexane=1:3 tochloroform:hexane=1:2) again, whereby a reddish brown solid wasobtained. The solid was suspended in a small amount of chloroform, anddiethyl ether was added to the suspension, followed by filtration. Afterthat, the resultant crystal was dried in a vacuum, and was thensubjected to sublimation purification, whereby 23.6 g (36.3 mmol, 40%yield) of Exemplified Compound No. A-1 was obtained.

Matrix-assisted laser desorption/ionization time-of-flight massspectrometry (MALDI-TOF MS) confirmed that the compound had an M+ of636.3.

The glass transition temperature of the compound in a glass state wasmeasured with a DSC (Pyris 1) manufactured by PerkinElmer from roomtemperature at a rate of temperature increase of 20° C./min. As aresult, the glass transition temperature was 196° C. In addition, thecompound was heated to its melting point. However, no recrystallizationwas observed, so it was confirmed that the compound was a materialhaving high glass property.

In addition, the structure of the compound was identified by NMRmeasurement.

¹H NMR(CDCl₃, 400 MHz) σ (ppm): 8.04 (d, 2H, J=7.6 Hz), 7.90 (d, 2H,J=6.7 Hz), 7.79 (m, 2H), 7.67 (m, 4H), 7.55 (m, 4H), 7.47-7.39 (m, 6H),7.24 (m, 2H), 6.71 (m, 2H), 1.59 (s, 6H), 1.57 (s, 6H).

In addition, a dilute solution of the compound in toluene having aconcentration of 1×10⁻⁵ mol/l was prepared, and the emission spectrum ofthe solution was measured with a fluorescence spectrophotometer F-4500manufactured by Hitachi, Ltd. In addition, the absorption spectrum ofthe solution was measured with an ultraviolet and visiblespectrophotometer V-560. Further, a solution of the compound inchloroform with its concentration adjusted to 0.1 wt % was applied ontoa glass substrate by spin coating, and the absorption spectrum andemission spectrum of the solution were measured. Then, the quantum yieldof the compound in a thin film was measured. The luminous wavelength ofbenzo[k]fluoranthene as a comparative substance was also measured.

TABLE 1 In a solution having a concentration of 1.0 × 10⁻⁵ mol/lLuminous wavelength Compound No. A-1 431 nm Benzo[k]fluoranthene 410 nm

TABLE 2 Thin film Luminous wavelength Compound No. A-1 449 nmBenzo[k]fluoranthene No light emission

In addition, the highest occupied molecular orbital (HOMO) energy of thecompound was measured by photoelectron spectroscopy (measuring devicename AC-1 manufactured by RIKENKIKI CO., LTD). The lowest unoccupiedmolecular orbital (LUMO) energy of the compound was calculated from ameasured value for an energy gap and the above HOMO energy. The HOMOenergy was −5.89 eV, and the LUMO energy was −2.98 eV.

Comparative Example 1

Synthesis of Comparative Compound 13

1.82 g (10.0 mmol) of Compound 8, 2.62 g (12.5 mmol) of Compound 9, and50 ml of ethanol were loaded into a 100-ml three-necked flask. In anitrogen atmosphere, the mixture was heated to 75° C., and was stirredfor 2 hours. The resultant solution was cooled, and was then filtrated.The resultant black solid was washed with 10 ml of methanol, whereby1.91 g (53.8% yield) of Compound 10 as a blackish green solid wereobtained.

1.0 g (2.91 mmol) of Compound 10, 0.55 g (4.00 mmol) of Compound 11, 3.0ml of isoamyl nitrite Compound 12, and 50 ml of tetrahydrofuran wereloaded into a 100-ml three-necked flask. In a nitrogen atmosphere, themixture was heated to 55° C., and was stirred for 4 hours. After thereaction, the resultant solution was condensed and purified with asilica gel column (heptane+toluene mixed developing solvent), whereby0.840 g (71.5% yield) of Comparative Compound 13 (whitish yellowcrystal) was obtained.

In addition, the structure of the compound was identified by NMRmeasurement.

¹H NMR(CDCl₃, 400 MHz) σ (ppm): 7.63-7.70 (m, 10H), 7.57 (d, 4H), 7.40(m, 2H), 7.32 (t, 2H), 7.61 (d, 2H).

The glass transition temperature of the compound in a glass state wasmeasured with a DSC (Pyris 1) manufactured by PerkinElmer from roomtemperature at a rate of temperature increase of 20° C./min, and theglass transition temperature was 96° C.

In addition, the luminous wavelength of the compound was measured by thesame approach as that of Example 1.

TABLE 3 In a solution having a concentration of 1.0 × 10⁻⁵ mol/lLuminous wavelength Compound No. A-1 431 nm Comparative Compound 13 420nm Benzo[k]fluoranthene 410 nm

FIG. 7 shows an emission spectrum in a solution.

The compound of the present invention has a luminous wavelength longerthan that of each of Comparative Compound 13 and benzo[k]fluoranthene.Accordingly, the compound may be a blue light emitting compound having awavelength appropriate for a light emitting device having highefficiency and good color purity when the compound is used in a display.

TABLE 4 Thin film Luminous wavelength Emission intensity Compound No.A-1 449 nm 1.93 Comparative Compound 13 429 nm 1.00 Benzo[k]fluorantheneNo light emission

FIG. 8 shows an emission spectrum in a thin film. The emissionintensities of two materials, that is, Compound No. A-1 and ComparativeCompound 13 were compared by using a wavelength of 354 nm, representedby the point of intersection of the absorption curves of the materialsat which the materials had the same absorbance, as an excitationwavelength. In addition, the thin film of benzo[k]fluoranthene was notobserved to emit light.

When the compound of the present invention is used as a light emittingmaterial in a light emitting device, the device is doped with thematerial at a concentration of about 0.1 to 20 wt % with respect to ahost material. Accordingly, the light emitting properties of the lightemitting material in a solid film are of extreme importance.

When the emission intensity of Comparative Compound 13 in a thin film isset to 1.0, Compound No. A-1 of the present invention has an emissionintensity of 1.93: Compound No. A-1 has a quantum yield about twice ashigh as that of Comparative Compound 13.

In addition, each of the HOMO energy and LUMO energy of each of CompoundNo. A-1 and Comparative Compound 13 was measured by the same approach asthat of Example 1.

TABLE 5 HOMO LUMO Compound No. A-1 −5.89 eV −2.98 eV ComparativeCompound 13 −5.91 eV −2.96 eV

Compound No. A-1 of the present invention may have improved holeinjecting property because the compound has HOMO energy larger than thatof Comparative Compound 13. In addition, Compound No. A-1 may haveimproved electron injecting property as well because the compound hasLUMO energy smaller than that of Comparative Compound 13. Accordingly,Compound No. A-1 may be a compound more appropriate for anelectroluminescence device than Comparative Compound 13.

Example 2

As the anode, a film of indium tin oxide (ITO) having a thickness of 120nm was formed on a glass substrate by a sputtering method, and theresultant was used as a transparent conductive supporting substrate. Theresultant substrate was subjected to ultrasonic cleaning in acetone andisopropyl alcohol (IPA) in this order. Then, the substrate was washed inboiling IPA and dried. The substrate was further subjected to UV/ozonecleaning to be used as a transparent conductive supporting substrate.

A chloroform solution of a compound represented by Compound 14 shownbelow was formed into a film having a thickness of 20 nm by a spincoating method on the transparent conductive supporting substrate,whereby a hole transporting layer was formed.

Further, the following organic layers and electrode layers werecontinuously formed by vacuum deposition based on resistance heating ina vacuum chamber having a pressure of 10⁻⁵ Pa, whereby a device wasproduced.

-   Light emitting layer (20 nm): Exemplified Compound No. A-1 (2% in    weight ratio): Compound 15    Electron transporting layer (30 nm): Bphen (manufactured by DOJINDO    LABORATORIES)    Metal electrode layer 1 (0.5 nm): LiF    Metal electrode layer 2 (150 nm): Al

The current-voltage characteristics of the resultant EL device weremeasured with a microammeter 4140 B manufactured by Hewlett-PackardCompany, and the emission brightness of the device was measured with aBM 7 manufactured by TOPCON CORPORATION. The device of this example wasobserved to emit light with an emission brightness of 957 cd/m² and aluminous efficiency of 2.9 lm/W at an applied voltage of 4.5 V. Inaddition, the device was observed to emit blue light having CIEchromaticity coordinates (x, y) of (0.15, 0.10) and good color purity.

Further, a voltage was applied to the device for 100 hours under anitrogen atmosphere. As a result, the device was observed to emit lightin a favorable manner continuously.

Example 3

A device was produced in the same manner as in Example 2 except thatCompound 16 was used instead of Compound 15 of Example 2. The device ofthis example was observed to emit light with an emission brightness of980 cd/m² and a luminous efficiency of 2.7 lm/W at an applied voltage of4.5 V. In addition, the device was observed to emit blue light havingCIE chromaticity coordinates (x, y) of (0.15, 0.10) and good colorpurity.

Further, a voltage was applied to the device for 100 hours under anitrogen atmosphere. As a result, the device was observed to emit lightin a favorable manner continuously.

As can be seen from Examples 2 and 3, a light emitting device using amaterial having a skeleton obtained by combining a benzo[k]fluorantheneskeleton and a fluorene skeleton is excellent from the viewpoints oflight emitting properties (a luminous wavelength and luminousefficiency), and heat stability. It has been also found that a lightemitting device using the above guest and a material having a skeletonobtained by combining a pyrene skeleton and a fluorene skeleton as ahost is excellent from the viewpoints of light emitting properties (aluminous wavelength and luminous efficiency), and durability.

Example 4

Synthesis of Exemplified Compound No. A-2

Exemplified Compound No. A-2 can be synthesized in the same manner as inExample 1 except that 2-iodo-9,9-diethylfluorene is used instead of2-iodo-9,9-dimethylfluorene of Example 1.

Example 5

Synthesis of Exemplified Compound No. A-3

Exemplified Compound No. A-3 can be synthesized in the same manner as inExample 1 except that 2-iodo-9,9-diisoprophylfluorene is used instead of2-iodo-9,9-dimethylfluorene of Example 1.

Example 6

Synthesis of Exemplified Compound No. A-54

Exemplified Compound No. A-54 was synthesized (15% synthesis yield) inthe same manner as in Example 1 except that 3-bromofluoranthene was usedinstead of 2-iodo-9,9-dimethylfluorene of Example 1.

Matrix-assisted laser desorption/ionization time-of-flight massspectrometry (MALDI-TOF MS) confirmed that the compound had an M+ of652.2.

In addition, the structure of the compound was identified by NMRmeasurement.

¹H NMR(CDCl₃, 400 MHz) σ (ppm): 8.26 (dd, 2H, J=7.5 Hz), 8.09 (m, 2H),8.02 (m, 4H), 7.91 (dd, 2H, J=15.7 Hz), 7.59 (m, 4H), 7.54-7.43 (m, 8H),7.32 (m, 2H), 7.10 (t, 2H, J=8 Hz), 6.37 (d, 2H, J=7 Hz).

In addition, a dilute solution of the compound in toluene having aconcentration of 1×10⁻⁵ mol/l was prepared, and the emission spectrum ofthe solution was measured with a fluorescence spectrophotometer F-4500manufactured by Hitachi, Ltd. The emission of blue light having goodcolor purity and a narrow half width was observed; the light had amaximum luminous wavelength of 447 nm and a half width of 70 nm.

Example 7

Synthesis of Exemplified Compound No. A-55

Exemplified Compound No. A-55 can be synthesized in the same manner asin Example 1 except that bromopyrene is used instead of2-iodo-9,9-dimethylfluorene of Example 1.

Example 8

Synthesis of Exemplified Compound No. A-56

Exemplified Compound No. A-56 can be synthesized in the same manner asin Example 1 except that 7-tertiary butyl-bromopyrene is used instead of2-iodo-9,9-dimethylfluorene of Example 1.

Example 9

Synthesis of Exemplified Compound No. A-5

Exemplified Compound No. A-2 can be synthesized in the same manner as inExample 1 except that 2-iodo-7-tertiary butyl-9,9-dimethylfluorene isused instead of 2-iodo-9,9-dimethylfluorene of Example 1.

Example 10

Synthesis of Exemplified Compound No. A-44

Exemplified Compound No. A-44 can be synthesized in the same manner asin Example 1 except that Compound 17 is used instead of2-iodo-9,9-dimethylfluorene of Example 1.

Example 11

An example of a method of producing a compound represented by thegeneral formula (I) in which R₇ and R₁₂ are different and each representsubstituents other than hydrogen atom is shown below.

In the formula, X represents a halogen atom. Compound 20 thus obtainedis subjected to a reaction in the same manner as in the section (1-3) ofExample 1, whereby a target product can be obtained.

Synthesis of Exemplified Compound No. A-20

Exemplified Compound No. A-20 can be synthesized by using bromobenzeneand 2-iodo-9,9-dimethylfluorene as Compound 18 and Compound 19 in theabove reaction formula, respectively.

Example 12

Synthesis of Exemplified Compound No. A-22

Exemplified Compound No. A-22 can be synthesized in the same manner asin Example 11 except that 3-bromotoluene is used instead of bromobenzeneof Example 11.

Example 13

Synthesis of Exemplified Compound No. A-24

Exemplified Compound No. A-24 can be synthesized in the same manner asin Example 11 except that 2-bromobiphenyl is used instead ofbromobenzene of Example 11.

Example 14

Synthesis of Exemplified Compound No. A-27

Exemplified Compound No. A-27 can be synthesized in the same manner asin Example 11 except that 1-bromonaphthalene is used instead ofbromobenzene of Example 11.

Example 15

Synthesis of Exemplified Compound No. A-32

Exemplified Compound No. A-32 can be synthesized in the same manner asin Example 11 except that 5-bromophenanthrene is used instead ofbromobenzene of Example 11.

Example 16

Synthesis of Exemplified Compound No. A-35

Exemplified Compound No. A-35 can be synthesized in the same manner asin Example 11 except that Compound 17 is used instead of bromobenzene ofExample 11.

Example 17

A device was produced in the same manner as in Example 2 except thatCompound 21 was used instead of Compound 15 of Example 2.

The device of this example was observed to emit blue light.

Example 18

Synthesis of Exemplified Compound No. A-70

Exemplified Compound No. A-70 was synthesized (9% synthesis yield) inthe same manner as in Example 1 except that2-bromo-9-methyl-9-trifluoromethylfluorene was used instead of2-iodo-9,9-dimethylfluorene of Example 1.

Matrix-assisted laser desorption/ionization time-of-flight massspectrometry (MALDI-TOF MS) confirmed that the compound had an M+ of744.2.

In addition, the structure of the compound was identified by NMRmeasurement.

¹H NMR(CDCl₃, 400 MHz) σ (ppm): 8.07 (d, 2H, J=7.6 Hz), 7.92 (m, 2H),7.88 (m, 2H), 7.78-7.65 (m, 8H), 7.56 (m, 2H), 7.46 (m, 4H), 7.26 (m,2H), 6.69 (m, 2H), 1.83 (s, 3H), 1.82 (s, 3H).

In addition, a dilute solution of the compound in toluene having aconcentration of 1×10⁻⁵ mol/l was prepared, and the emission spectrum ofthe solution was measured with a fluorescence spectrophotometer F-4500manufactured by Hitachi, Ltd. The emission of blue light having goodcolor purity and a narrow half width was observed; the light had amaximum luminous wavelength of 448 nm and a half width of 61 nm.

Example 19

A device was produced in the same manner as in Example 2 except thatExemplified Compound No. A-54 was used instead of Exemplified CompoundNo. A-1 of Example 2. The device of this example was observed to emitlight with an emission brightness of 130 cd/m² at an applied voltage of4.5 V, and current efficiency and power efficiency were 4.0 cd/A and 2.7lm/W, respectively. In addition, the device was observed to emit bluelight having CIE chromaticity coordinates (x, y) of (0.15, 0.13) andgood color purity.

Further, a voltage was applied to the device for 100 hours under anitrogen atmosphere. As a result, the device was observed to emit lightin a favorable manner continuously.

Example 20

A device was produced in the same manner as in Example 2 except thatExemplified Compound No. A-70 was used instead of Exemplified CompoundNo. A-1 of Example 2. The device of this example was observed to emitlight with an emission brightness of 570 cd/m² at an applied voltage of4.5 V, and current efficiency and power efficiency were 3.7 cd/A and 2.4lm/W, respectively. In addition, the device was observed to emit bluelight having CIE chromaticity coordinates (x, y) of (0.15, 0.09) andgood color purity.

Further, a voltage was applied to the device for 100 hours under anitrogen atmosphere. As a result, the device was observed to emit lightin a favorable manner continuously.

Example 21

Synthesis of Exemplified Compound No. A-33

5.97 g (18.3 mmol) of 3-bromofluoranthene and 200 mL of diethyl etherwere added to a 300 mL reaction vessel. The solution was cooled to −78°C., and 11.6 mL (18.3 mmol) of a solution of n-butyllithium in hexanehaving a concentration of 1.57 mol/L were added to the solution over 10minutes. After the solution had been stirred at the temperature for 30minutes, Compound 22 (5.15 g, 18.3 mmol) dissolved in 50 mL of diethylether was added to the solution in one stroke. The solution was heatedto room temperature while a cooling bath was attached, and 100 mL of a10% aqueous solution of ammonium chloride were added to the suspension,followed by extraction with ethyl acetate (100 mL×twice). An organiclayer was collected, washed with distilled water and a saturated saltsolution, and dried with anhydrous MgSO₄. After that, the solution wascondensed and dried in a high vacuum, whereby a tan solid compound wasobtained.

The resultant solid compound was loaded into a 500 mL reaction vessel,and 100 mL of xylene, 1.56 g (8.19 mol) of p-toluenesulfonic acid, and4.17 g (27.4 mmol) of acenaphthylene were added to the vessel. Thesolution was vigorously stirred at 150° C. for 36 hours. Xylene wasremoved under reduced pressure, and 100 mL of saturated sodiumbicarbonate water and 100 mL of distilled water were added to thesolution, followed by extraction with chloroform (100 mL×twice). Anorganic layer was collected, washed with saturated sodium bicarbonatewater, distilled water, and a saturated salt solution, and dried withanhydrous MgSO₄. After that, the desiccant was separated by filtration.After the filtrate was condensed, a black silica gel carrier wasobtained. The carrier was purified by means of silica gel columnchromatography (mobile phase; chloroform:hexane=1:3 tochloroform:hexane=1:1), whereby a reddish brown solid was obtained. Thesolid was suspended in a small amount of chloroform, and diethyl etherwas added to the suspension to precipitate a crystal. The crystal wastaken by filtration and purified by means of silica gel columnchromatography (mobile phase; chloroform:hexane=1:3 tochloroform:hexane=1:2) again, whereby a reddish brown solid wasobtained. The solid was suspended in a small amount of chloroform, anddiethyl ether was added to the suspension, followed by filtration. Afterthat, the resultant crystal was dried in a vacuum, and was thensubjected to sublimation purification, whereby 2.5 g (3.88 mmol, 21%yield) of Exemplified Compound No. A-33 were obtained.

Matrix-assisted laser desorption/ionization time-of-flight massspectrometry (MALDI-TOF MS) confirmed that the compound had an M+ of644.3.

INDUSTRIAL APPLICABILITY

The compound represented by the general formula (I) of the presentinvention has a high glass transition temperature and high thin-filmstability. Accordingly, the compound can be used as a guest for thelight emitting layer of an organic light emitting device capable ofemitting blue light with high brightness and good color purity at a lowapplied voltage.

While the present invention has been described with reference toexemplary embodiments, it is to be understood that the invention is notlimited to the disclosed exemplary embodiments. The scope of thefollowing claims is to be accorded the broadest interpretation so as toencompass all such modifications and equivalent structures andfunctions.

This application claims the benefit of Japanese Patent Application Nos.2006-099896, filed Mar. 31, 2006, and 2006-334985, filed Dec. 12, 2006,which are hereby incorporated by reference herein in their entirety.

1. A display comprising a substrate and an organic light emittingdevice, the organic light emitting device comprising a pair ofelectrodes formed of an anode and a cathode, and an organic compoundlayer interposed between the pair of electrodes, wherein the organiccompound layer contains a compound, the compound being represented bythe following general formula (I):

wherein R₁, R₂ and R₅ to R₁₂ each represent a hydrogen atom, a linear orbranched alkyl group, a substituted or unsubstituted aryl group, or asubstituted or unsubstituted heterocyclic group; wherein R₃ and R₄ eachrepresent a hydrogen atom, provided that at least one of R₇, R₈, and R₉and at least one of R₁₀, R₁₁, and R₁₂ represent a substituted orunsubstituted condensed ring aromatic group, which is tricyclic or more;and wherein R₇ in the general formula (I) represents a substituted orunsubstituted fluoranthenyl group.
 2. A display comprising an organiclight emitting device, the organic light emitting device comprising apair of electrodes formed of an anode and a cathode, and an organiccompound layer interposed between the pair of electrodes, wherein theorganic compound layer contains a compound, the compound beingrepresented by the following general formula (IV):

wherein R₁, R₂, R₅, R₆, and R₈ to R₁₂ each represent a hydrogen atom, alinear or branched alkyl group, a substituted or unsubstituted arylgroup, or a substituted or unsubstituted heterocyclic group; wherein R₃and R₄ each represent a hydrogen atom, provided that at least one ofR₁₀, R₁₁, and R₁₂ represents a substituted or unsubstituted condensedring aromatic group, which is tricyclic or more; wherein R₂₉ and R₃₀each represent a hydrogen atom, an alkyl group, a substituted orunsubstituted aryl group, a substituted or unsubstituted heterocyclicgroup, a substituted amino group, or a halogen atom; wherein erepresents an integer of 1 to 5, and f represents an integer of 1 to 4;and when the number of any one of R₂₉ and R₃₀ is two or more, R₂₉'s orR₃₀'s may be identical to or different from each other.
 3. A displaycomprising an organic light emitting device, the organic light emittingdevice comprising a pair of electrodes formed of an anode and a cathode,and an organic compound layer interposed between the pair of electrodes,wherein the organic compound layer contains a compound, the compoundbeing represented by the following general formula (V):

wherein R₁, R₂, R₅, R₆, and R₈ to R₁₁ each represent a hydrogen atom, alinear or branched alkyl group, a substituted or unsubstituted arylgroup, or a substituted or unsubstituted heterocyclic group; wherein R₃and R₄ each represent a hydrogen atom; wherein R₂₉ to R₃₂ each representa hydrogen atom, an alkyl group, a substituted or unsubstituted arylgroup, a substituted or unsubstituted heterocyclic group, a substitutedamino group, or a halogen atom; wherein e and g each represent aninteger of 1 to 5, and f and h each represent an integer of 1 to 4; andwhen the number of any one of R₂₉, R₃₀, R₃₁, and R₃₂ is two or more,R₂₉'s, R₃₀'s, R₃₁'s, or R₃₂'s may be identical to or different from eachother.
 4. The display according to any one of claims 1-3, wherein theorganic compound layer comprises a light emitting layer.
 5. The displayaccording to claim 4, wherein the light emitting layer is formed of atleast two kinds of compounds including a host and a guest, and saidguest is a compound represented by the general formula (I).
 6. Thedisplay according to claim 4, wherein the light emitting layer is formedof at least two kinds of compounds including a host and a guest, andsaid guest is a compound represented by the general formula (IV).
 7. Thedisplay according to claim 4, wherein the light emitting layer is formedof at least two kinds of compounds including a host and a guest, andsaid guest is a compound represented by the general formula (V).
 8. Thedisplay according to claim 4, wherein the organic light emitting deviceemits a blue light.